Diethyl isocyanomethylphosphonate
Diethyl isocyanomethylphosphonate (CAS 41003-94-5), with the linear formula CNCH2P(O)(OC2H5)2 and a molecular weight of 177.14 g/mol, is a valuable synthetic reagent. It is employed in various chemical transformations, including copper-catalyzed cycloaddition reactions and the preparation of complex organic molecules such as steroidal analogs and diamide prodrugs.
- IUPAC
- Isocyanomethylphosphonic acid diethyl ester
- Synonyms
- Isocyanomethylphosphonic acid diethyl ester
Copper-Catalyzed Cycloaddition Reactions
This compound serves as a reactant in copper-catalyzed cycloaddition reactions, facilitating the formation of new cyclic structures.
Preparation of Glucose-Lowering Prodrugs
It is utilized in the preparation of orally bioavailable diamide prodrugs designed to lower glucose levels in diabetic animal models by inhibiting fructose-1,6-bisphosphatase.
Synthesis of Antifungal Agents
Diethyl isocyanomethylphosphonate is employed in the synthesis of sterol analogs that exhibit antifungal activity against plant pathogens.
Asymmetric Synthesis of Steroidal Diketopiperazines
The reagent is a key component in the asymmetric synthesis of steroidal 2,5-diketopiperazines, leveraging stereoselective Ugi four-component condensation.
Passerini Reaction
It participates in the Passerini reaction, a multicomponent reaction used in organic synthesis for the creation of alpha-acyloxy carboxamides.
| Molecular weight | 177.14 |
|---|---|
| Linear formula | CNCH2P(O)(OC2H5)2 |
| Assay | 97% |
| Boiling point | 84-87 °C/0.1 mmHg(lit.) |
| Density | 1.105 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.433(lit.) |
| Storage temperature | 2-8°C |
| Application | Reactant for:• Copper-catalyzed cycloaddition reactions1• Preparation of orally bioavailable diamide prodrugs that lower glucose in diabetic animals through inhibition of fructose-1,6-bisphosphatase2• Synthesis of sterol analogs as antifungal agents against plant pathogens3• Asymmetric synthesis of steroidal 2,5-diketopiperazines prepared via isocyanide chemistry based on stereoselective Ugi four component condensation and subsequent cyclocondensation reactions4• The Passerini reaction5 |
Hazard statements
- H302Harmful if swallowed
- H315Causes skin irritation
- H319Causes serious eye irritation
- H335May cause respiratory irritation
Precautionary statements
- P261Avoid breathing dust, fume, gas or vapours
- P280Wear protective gloves, clothing and eye/face protection
- P305IF IN EYES
| Protective equipment | Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter |
|---|---|
| Flash point | 113 °C / 235.4 °F |
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xn |
| Risk statements (R) | 20/21/22-36/37/38 |
| Safety statements (S) | 26-36 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is Diethyl isocyanomethylphosphonate used for?
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Diethyl isocyanomethylphosphonate is used as a reactant in copper-catalyzed cycloaddition reactions, for the preparation of orally bioavailable diamide prodrugs, synthesis of sterol analogs as antifungal agents, asymmetric synthesis of steroidal 2,5-diketopiperazines, and in the Passerini reaction.
What is the CAS number and formula for Diethyl isocyanomethylphosphonate?
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The CAS number is 41003-94-5 and the linear formula is CNCH2P(O)(OC2H5)2.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies Diethyl isocyanomethylphosphonate with an assay of 97%. We do not represent this product as USP, BP, EP, or any other pharmacopoeia grade.
How should Diethyl isocyanomethylphosphonate be handled safely?
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Diethyl isocyanomethylphosphonate is a warning substance that is harmful if swallowed, in contact with skin, or if inhaled. It also causes skin irritation, serious eye irritation, and may cause respiratory irritation. Appropriate personal protective equipment, including eyeshields, gloves, and a suitable respirator, should be used. Ensure adequate ventilation.
Is Diethyl isocyanomethylphosphonate available for export?
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Yes, Tech Serve Solutions is a specialist global supplier and exporter of fine chemicals, including Diethyl isocyanomethylphosphonate. We can facilitate international orders.
How can I request a quote or sample?
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To request a quote or a sample of Diethyl isocyanomethylphosphonate, please contact our sales department through our website or by phone, providing your specific requirements.
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